Boron trifluoride etherate → 2-Hydroxy-4,5-dimethoxybenzoic acid

HRID 78697

反応式

HRID 78697 の反応式
C[O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Na+].[Br-].B(F)(F)F.CCOCC.[OH-].[Na+]>C(OCC)(=O)C.O>[OH:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

参加物

7

反応物 4

HCID 8000Boron trifluoride etherateHCID 102762,4,5-Trimethoxybenzoic acidHCID 14798Sodium HydroxideHCID 253881Sodium Bromide

生成物 1

HCID 115646502-Hydroxy-4,5-dimethoxybenzoic acid収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

In 10 g of ethyl acetate were suspended 2.0 g of 2,4,5-trimethoxybenzoic acid (1a) and 1.45 g of NaBr in a stream of argon, to which 4.0 g of BF3.Et2O was then added dropwise at 25° C., followed by heat stirring at 40° C. for 3 hours. The reaction mixture was cooled with ice, to which 10 mL of water was then added dropwise at 10° C., followed by dropwise adding 7.5 g of a 25% (w/w) sodium hydroxide aqueous solution. Thereto was further added 10 mL of water before stirring, followed by filtering off insoluble inorganic matter. To the separated aqueous layer was dropwise added 3.94 g of 35% hydrochloric acid, followed by stirring for 10 minutes. The precipitated crystal was collected by filtration and washed with water. The resultant crystal was then dried under reduced pressure at 60° C. to provide 1.7 g of 2-hydroxy-4,5-dimethoxybenzoic acid (2a) at a yield of 91%.

後処理

  1. temperatureby heat
  2. additionwas then added dropwise at 10° C.
  3. stirringbefore stirring
  4. filtrationby filtering off insoluble inorganic matter
  5. stirringby stirring for 10 minutes
  6. filtrationThe precipitated crystal was collected by filtration
  7. washwashed with water
  8. customThe resultant crystal was then dried under reduced pressure at 60° C.

出典と根拠

ORDレコード
ord-a5126c13cb174211811fcc74d1968deb
出典データセット
uspto-grants-2014_09
特許番号
US08841461B2

関連ノート

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